


Tender Spot

by Anonymous



Category: Supernatural
Genre: Aftercare, Anal Speculum, BDSM Scene, Butt Plugs, Caning, Figging, Fully Planned Out BDSM Scene, Hand Jobs, M/M, Object Insertion, Orgasm Denial, POV First Person, Spreader Bars, Tied-Up Dean Winchester
Language: English
Status: Completed
Published: 2019-04-07
Updated: 2019-04-07
Packaged: 2020-01-06 05:44:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,387
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18382163
Author URL: https://archiveofourown.org/
Summary: Dean needs to let go, but it’s never easy to find a way out of his head for a while.He finds someone to help him with that.





	Tender Spot

**Author's Note:**

> See the end notes for the SPN Kink Meme Prompt.

I’ve been in this business a long time, and you know seen a lot of weird shit, done more, but sometimes something comes along and it’s a total WTF moment.

Like now. The blonde guy’s holding back the curtain and pointing across the street to another guy.

The guy with me is big. The other guy: he’s huge, way over six foot and looking like he could punch through metal.

“That,” the blonde guy says, “is my brother. You cross a line in here, or I don’t give him the safe signal in twenty minutes, or I don’t walk out of here, he will hunt you down and kill you. And we do that for a living, so you better know I’m serious.”

He is, I can tell just by looking at him. He’s not trying to sound hard, like some kind of badass. He says it so matter of fact that I’m pretty sure these are two I don’t want to mess with.

But this guy has just put three hundred bucks on the table, for some very specific action, and I’m not about to pass up that cash.

“Fine,” I agree. “So strip already, and get on the bed. In position.”

I look out one last time at the giant across the street, see him glaring back, and then close the curtain over.

The good thing about Billy’s motel is that he can keep his mouth shut. You see him right, toss him a cut, and he’ll lie to his own grandma for you, and even clean out the room once you’re done.

It makes the motel a good place to bring custom, and, since probably most of the rooms are being used for the same thing, nobody cares about the noise.

Freckles is on the bed, ass in the air, forehead resting on his folded arms.

I pick up the cane he brought with him, give it a few exploratory swipes, listen to it whistle through the air.

Fuck, this he is going to feel.

I move to stand behind him, and tap the small of his back with the end of the cane. “Cute you think I’m doing all the work here. Get those cheeks spread.”

He grumbles, ends up with his weight balanced on the side of his face, and reaches back to grab handfuls of his own ass.

Tugs, and shows me the target.

His fingers are leaving white spots of pressure where he’s digging in, and I know that’s going to hurt after a while.

But it’s his three hundred bucks, and that’s nothing to what’s coming next, so…

I keep the first couple of swipes light, let him get used to it. Once I weigh in, once his hole really gets warm, it’s going to hurt a whole lot, and these taps’ll let him know it.

He’s panting by number six, and then the mouth starts, which I was kind of expecting; he’s got the look of a sassy little shit about him.

“You hit like a ninety pound weakling,” he says. “Earn that fucking money.”

I keep it the same pace just to piss him off, know what he’s trying to drive me to do, but holding back is punishment in itself, and we’ll get there soon enough.

Just when he’s about to backchat me some more, I let him have it, smack that cane right across his bud so hard I feel my own palm sting as well.

He makes a choked gasp, the words he was going for lost in it somewhere, and a deep flush colours his face.

Yeah, like he said. I’ll earn that money.

I don’t show him any mercy, after that. My aim is spot on, and every single strike of the cane hits its target, whipping the flesh into something swollen and red hot looking, and it falls into a pattern.

Swish. Crack. The sound he makes as he tries to pull in air through the pain.

Swish. Crack. Pant.

Swish. Crack - 

“Stop, fucking stop,” he begs, but that isn’t the way this is to go, he was damn clear.

Thirty full on swipes, and we’re at twenty five. (I don’t go with that getting the sub to count shit, if you’re in charge then be in charge).

I give him the last five lightning style, and then put the cane down beside him, the signal that part’s done.

He flops down onto his side, drenched in sweat, breathing so hard he looks like he’s been running for his damn life.

I look at my watch; near enough the twenty minute part.

“You wanna give your brother that signal? Because once we get started again, you’re not getting off that bed.”

He looks at me, a little desperate, like getting up is something he just can’t do, but I fold my arms and jerk my head towards the window.

He moans, but clambers awkwardly off the bed and hobbles over.

Twitches the curtain so, I guess, to spare his brother from seeing more than he has to.

I don’t know what signal he gives, but then he puts the curtain back in place, and stiffly turns around.

“Bed,” I tell him. “Lie on your front, hands behind your back.”

While he struggles to do it, moaning at the pain in his ass, I start going through the bag he brought with him.

Yeah, guy came prepared; there’s everything in here I’ll need to give him what he wants.

I grab the cuffs first, and turn to find he’s done what I said. 

Lying on his stomach, hands pressed into the small of his back, fingers curled in.

“Good boy,” I tell him, and it’s interesting watching his face. There’s a mini war going on there; half of him seems to want to bask in what I said, but there’s a fuck you in his eyes. I grin. Oh, breaking him of that is going to be fun.

He holds still while I fasten the cuffs on, and then I grab the ankle cuffs and spreader bar from the bag.

I set the width so his legs will be stretched to the maximum, and put on the cuffs before fastening the bar into place.

“Look at you. All laid out for me, all helpless. Do you think your brother’s still out there? Maybe he found some company. Maybe he’s left you all alone and unprotected. I could do what I wanted, now, huh. And nobody would be coming to save you.”

He tries to move, to turn over, but he’s going nowhere. I let him try, watch him struggling and cursing, and finally the fight drains out of him.

“He’ll kill you,” he threatens. “I’ll kill you.”

I’m just following the script, and he is too, but the venom when he says that leaves me in no doubt that he isn’t kidding.

Just as well I’ve no plans to deviate from what we agreed, threats of painful demise notwithstanding.

This sub’s put his trust in me, and I would never, ever betray that.

I pull the bag up onto the bed so I don’t have to keep going back and forth to it, and lay out what I’m going to use next.

Right where he can see, and his eyes go wide.

“Hell, no, wait…”

“No, I don’t think so.”

I pull on some gloves and lube up my fingers thoroughly, and slip just the tip of one inside that poor abused hole.

He actually squeals and tries to buck away, but we both know he’s going nowhere.

What follows as I open him up doesn’t even sound human after a bit. Words, threats, curses turn into whines and moaned pleas, but I keep going, sometimes, pulling out to drag my finger around his hole, pressing on the spots that look sorest.

Tears are welling up in his eyes, but he’s fighting them.

“Might as well let go,” I tell him. “It gets worse from here on in.”

I pick up the toy he’s brought. Starts thin, almost tapered, widens towards a pretty impressive base. That is going to hurt, and I insert it nice and slow so he feels every painful inch of stretch.

Once it’s seated, I turn it on, all the way, and he starts jabbering, and begging again, and I just let him.

I watch him careful though; he’ll get to come but not this time, and when he’s humping the bed, desperate for some kind of friction to get his release, I turn off the toy and take it out.

His hole twitches, and that stretched, swollen ring looks so tempting.

I finger it a little, pinching and rubbing, and he’s back to trying to pull away again, cursing and yelping, until he runs out of steam and just has to lie there while I play with him some more.

But the best is yet to come, and I make sure he sees the speculum when I lift it to to apply some lube.

“You’re not putting that in me.”

I lean forward, grinning. “Don’t really think you’re in a position to do much about it.”

The minute the cold metal touches him he nearly has a fit, jerking and trying to pull away.

I gotta admire his fight, but he really is going nowhere, and I’m out of patience, so I put the speculum down and spank his hole with my hand for a minute until he gets the message.

Then, when he’s panting hard enough to shake the bed, I lean over him so he can see my face.

“You keep trying me, boy, I’ll shove my dick down your throat until you pass out and then I’ll bring you around and do it again. You want that?”

He shakes his head, frantic, and I go back to where I was.

This time, the fight to keep himself still is obvious in every taut trembling line of his body.

I take my time inserting the speculum, loving every pained moan that comes from him.

I open it just wide enough for the ginger though, a good sized chunk, peeled down, fresh thanks to the zip loc bag he put it in, with a big part of the root still attached

When he feels that first sting he screams, but then turns his head into the pillow to stifle it.

I tsk him as I close the speculum, watching his channel seal itself around that burning intrusion.

“Nobody cares here. You scream all you want, I promise you, people are used to to it.”

That isn’t always a good thing, but Billy mostly keeps the real bad guys away, another reason this is my favourite place to bring clients.

Then I sit back to watch. His struggles are beautiful, trying and failing to push the ginger out, and he is crying now, fat tears streaming down his cheeks as he begs some more.

But we both know it isn’t coming out until the time’s up.

The juice from the ginger’s on my gloves, and I rub it around his hole, smearing it especially where the flesh looks redder, sorer.

He sobs at me when I do that, and those freckles stand out beautifully against his flushed cheeks.

“Ssh,” I soothe him. “Just a little longer, then we’re almost done.”

After a few minutes, and I have to put my hand on the small of his back to hold him in place, I grab the root of the ginger and pull.

Slowly, edging it out until it pops clear. I hold it against his hole for a moment, knowing it’ll burn, but he’s so far gone at that point he can only jerk and twitch.

I put it back in the bag, and the pick up the final toy. It’s an inflatable butt plug, and I hold it in front of his face.

“Nearly there. You’ve been so good for me, Dean. So good. One last thing, okay? Then you get to come.”

He nods, the finish line in sight making his torment bearable.

I slide it in, inflate it until it’s snug, secure, and then I unfasten the spreader bar and set it aside.

I hook the leg cuffs together, and then carefully turn him over.

I pull on a fresh pair of gloves - ginger juice on his dick wasn’t on the list - and start jacking him off.

He groans and jerks as I push him towards that edge, fast and nasty, and he’s more than ready for it; the pain has ramped him up and it just takes my a few more rough strokes and then he’s coming, spurting over my gloved hand.

I wait until his breathing’s settled, and then undo the cuffs, and grab a washcloth to clean him up, but the plug…. That stays in, like he told me.

After, I hold him, let him rest up against me. He comes back out of it slowly, and it’s like all the tension he was wearing when he walked in is gone.

There’s some OJ and chocolate in the mini fridge and I get him to take both before watching him carefully as he gets dressed.

“Your brother, he’ll keep an eye on you?”

Dean’s putting everything back in the bag. “Yeah, he knows what to look out for. We’ve been, uh, around this block a few times.”

I don’t ask him any more questions. It’s not my business, so long as I know he won’t be alone.

He goes to the window, pulls back the curtain, and I can see Sam is still out there.

As he leaves, Dean looks back at me.

“If.. If I called you, again…. Would you….”

I nod. It’d be good for him to have someone he can trust to stay within the lines, and three hundred bucks isn’t anything to turn my nose up at.

“Any time.”

Then he’s gone. Back to his brother, and into a sleek black muscle car that growls its way into the night.

I pick up the cash, pocket it, and look around to make sure neither of us left anything behind.

I get the impression Dean did, but then maybe it was something he could only slough in here, and if I helped with that?

Yeah, a good night’s work.

**Author's Note:**

>  _Someone - I don't really care who, so feel free to pick who you want - spanks or canes Dean's hole until it's puffy, red and sore. Afterwards, they spend some time playing with it while it's still sore, enjoying the pained gasps from Dean. That might include fingering, toys, fisting, fucking him, figging for some more pain... I'm open to pretty much everything except scat or gore so yeah._  
>  Also not at all required but I'd love it if at the end of it all they filled Dean's hole with an inflatable plug (inflated, ofc) to keep him nice and stretched and full.


End file.
